Rh‐Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E

• Published in: European journal of organic chemistry Vol. 2019; no. 46; pp. 7545 - 7554
• Main Authors: Rao, Maddali L. N., Ramakrishna, Boddu S.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 15-12-2019
• Subjects: Decarbonylative addition; Functional groups; Ketones; o‐Hydroxydihydrochalcones; Rhodium; Rhodium catalysis; Salicylaldehyde; Selectivity
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201901314

A rhodium‐catalyzed decarbonylative addition of salicylaldehydes with vinyl ketones was developed to synthesize o‐hydroxydihydrochalcones (2‐hydroxyphenethyl ketones). These decarbonylative addition reactions afforded various functionalized o‐hydroxydihydrochalcones in moderate to good yields with broad functional group tolerance and selectivity. This method was also applied further in the divergent synthesis of dihydrochalcone derived taccabulins A–E.
A Rh‐catalyzed decarbonylative addition of salicylaldehydes with vinyl ketones was developed for the synthesis of o‐hydroxydihydrochalcones in good yields. This protocol was applied in the synthesis of taccabulin family of natural products.